Senior AI Engineer, Gen AI

Senior AI Engineer, GenAI

Chicago, Illinois

Honeycomb Insurance

At Honeycomb, we’re not just building technology; we’re reshaping the future of insurance.

In 2025, Honeycomb was recognized by Dun & Bradstreet as “Top 10 Best Start Up Companies to Work For” in Israel, named by LinkedIn as “Top 10 Startups in Chicago”, and Newsweek’s “Greatest Startup Workplaces in America, 2025”. Through the first half of 2026 we’ve been recognized on Inc. Magazine’s “Best Workplaces” List and Forbes “Fintech 50”.

How did we earn these honors?

Honeycomb is a rapidly growing global startup, generously backed by top-tier investors and powered by an exceptional team of thinkers, builders, and problem-solvers. Dual-headquartered in Chicago and Tel Aviv (R&D center), and with 6 offices across the U.S., we are reinventing the commercial real estate insurance industry, an industry long overdue for disruption. Just as importantly, we ensure every employee feels deeply connected to our mission and one another.

With over $100B in insured assets, Honeycomb operates across 23 states, covering more than 65% of the U.S. population and increasing its coverage.

If you’re looking for a place where innovation is celebrated, culture actually means something, and smart people challenge you to be better every day — Honeycomb might be exactly what you’ve been looking for.

As a Senior AI Engineer (GenAI), you will own production GenAI systems end-to-end, from the eval set, to the agent design, to the FastAPI handler running in production, to the dashboard you check the next morning.

You’ll work directly on systems like our customer support agent, which today drafts replies to real customers and CS reps in a regulated insurance setting — no toy demos, no handoff to a separate engineering team.

This is a high-ownership role where your work directly influences our products, operations, and long-term AI strategy.

• Design, build, and ship agentic AI workflows end-to-end — agent logic, RAG, FastAPI service, deployment, monitoring
• Build and own evaluation pipelines: golden datasets, LLM-as-judge calibration, regression tests, distribution-shift detection
• Productionize RAG pipelines grounded in insurance-specific data
• Integrate LLM agents with policy/claims systems and internal tools
• Own observability, guardrails, safety, and error handling for systems serving real users
• Build automations that take repetitive operational work off the team’s plate, including agent Skills and browser-use tooling where it speeds delivery

• 6+ years in AI/ML, Data Science, or applied engineering; 1–3 years shipping production GenAI applications (LLMs, agents, RAG) — not demos
• Master’s or PhD in CS, ML, Statistics, Engineering, or related, or equivalent practical experience
• Hands-on with multi-agent orchestration, tool use, and context-managed conversational systems (OpenAI Agents SDK, LangGraph, or similar)
• Deep expertise in RAG, vector databases, embedding selection, and retrieval optimization
• Strong Python + ML foundations (PyTorch, scikit-learn, Hugging Face)

Nice to have

• Experience building automations and agent Skills, or working with browser-use agents to automate real workflows

• Salary. Range: 170K - 210K
• ISO stock options
• Medical, dental, and vision coverage for you and your dependents
• HSA with company contributions
• 401(k) with employer match
• Flexible time off 
• 10 company-paid holidays
• Paid family leave 

Honeycomb is committed to fair and equitable compensation practices. The base salary range listed in each job posting represents our good faith estimate of what we expect to pay for the role. Actual compensation may vary based on skills, experience, education, and location, as well as internal alignment and market factors.